Born in 1961 in Cork, Ireland, Spillane graduated from University College Cork and got his professional music start during the 1980s with the Stargazers, an Irish trio in which he performed for several years and for which he penned a couple songs. He then more notably spent several years as a bandmember of Nomos, appearing on the albums I Won't Be Afraid Anymore (1995) and Set You Free (1997) and penning the much-covered song "All the Ways That You Wander" for the former album. Spillane subsequently made his full-length album solo debut in 1997 with The Wells of the World, followed by Will We Be Brilliant or What? (2002), Hey Dreamer (2005), and My Dark Rosaleen & the Island of Dreams (2008). Furthermore, in 2003 Spillane won the Meteor Ireland Music Award for Best Folk/Traditional Act, and in 2006 he and frequent songwriting partner Louis de Paor collaborated on the album The Gaelic Hit Factory.

Artists who have covered Spillane's songs over the years include Méav ("When You and I Were True," 1998; "You Brought Me Up," 2002), Solas ("Sraid an Chloig," 1998), Maca ("Rinn na Mara," 1998), Máire Ní Chéilleachair ("All the Ways You Wander," 1999), Sinéad Lohan ("Eist do Bheal," 1999), Karan Casey ("We're Going Sailing," 2000; "Buile Mo Chroi," "You Brought Me Up," 2001; "Song of Lies," "Bata is Bóthar," 2003), Christy Moore ("Johnny Don't Go," 2001; "Magic Nights in the Lobby Bar," 2005), Sharon Shannon ("All the Ways You Wander," 2003), Seán Keane ("Valley of the Heart," "The Only One for Me," "The Land You Love the Best," 2003), Pauline Scanlon ("All the Ways You Wander," 2004; "When You and I Were True," 2006), George Murphy ("The Moon Going Home," "The Land You Love the Best," 2004), Shanneyganock ("I'm Gonna Set You Free," 2004), Cathie Ryan ("The Wild Flowers," 2005), Michelle Lally ("All the Ways You Wander," 2006), Rory McCarthy ("Ireland Free," 2006), and Róisín Elsafty ("Poor Weary Wanderer," 2006). ~ Jason Birchmeier